Selecting Enterprise Email Security: the Buying Process

To wrap up this series we will bring you through a process of narrowing down the shortlist and then testing products and/or services in play. With email it’s less subjective because malicious email is… well, malicious. But given the challenges of policy management at scale (discussed in our last post), you’ll want to ensure a capable UX and sufficient reporting capabilities as well. Let’s start with the first rule of buying anything: you drive the process. You’ll have vendors who want you to use their process, their RFP/RFP language, their PoC guide, and their contract language. All that is good and well if you want to buy their product. But what you want is the best product to solve your problems, which means you need to drive your selection process. We explained in our introduction that a majority of attacks start with a malicious email. So selecting the best platform remains critical for enterprises. You want to ensure your chosen vendor addresses the email-borne threats of not just today, but tomorrow as well. A simple fact of the buying process is that no vendor ever says “We’re terrible at X, but you should buy us because Y is what’s most important to you.” Even though they should. It’s up to you to figure out each vendor’s real strengths and weaknesses and line them up against your requirements. That’s why it’s critical to have a firm handle on your requirements before you start talking to vendors. The first step is to define your short list of 2-3 vendors who appear to meet your needs. You accomplish this by talking to folks on all sides of the decision. Start with vendors but also talk to friends, third parties (like us), and possibly resellers or managed service providers. When meeting vendors stay focused on how their tool addresses your current threats and their expectations for the next wave of email attacks. Make any compliance or data protection issues (or both) very clear because they drive the architecture and capabilities you need to test. Don’t be afraid to go deep with vendors. You will spend a bunch of time testing platforms, so you should ask every question you can to make an educated decision. The point of the short list is to disqualify products that won’t work early in the process so you don’t waste time later. Proof of Concept Once you have assembled the short list it’s time to get hands-on with the email security platforms and run each through its paces through a Proof of Concept (PoC) test. The proof of concept is where sales teams know they have a chance to win or lose, so they bring their best and brightest. They raise doubts about competitors and highlight their own capabilities and successes. They have phone numbers for customer references handy. But forget all that now. You are running this show, and the PoC needs to follow your script – not theirs. Preparation Vendors design PoC processes to highlight their product strengths and hide weaknesses. Before you start any PoC be clear about the evaluation criteria. Your criteria don’t need to be complicated. Your requirements should spell out the key capabilities you need, with a plan to further evaluate each challenger based on squishier aspects such as set-up/configuration, change management, customization, user experience/ease of use, etc. With email it all starts with accuracy. So you’ll want to see how well the email security platforms detect and block malicious email. Of course you could stop there and determine the winner based on who blocks 99.4%, which is better than 99.1%, right? Yes, we’re kidding. You also need to pay attention to manageability at scale. The preparation involves figuring out the policies you’ll want to deploy on the product. These policies need to be consistent across all of the products and services you test. Here are some ideas on policies to think about: Email routing Blocked attacks (vs. quarantined) Spam/phishing reporting Email plug-in Threat intelligence feeds to integrate Disposition of email which violates policy Attributes requiring email encryption Integration with enterprise security systems: SIEM, SOAR, help desk And we’re sure there are a bunch of other policy drivers we missed. Work with the vendor’s sales team to make sure you can exercise each product or service to its fullest capabilities. Make sure to track additional policies, above and beyond the policies you defined for all the competitors – you want an apples to apples comparison, but also want to factor in additional capabilities offered by any competitors. One more thing: we recommend investing in screen capture technology. It is hard to remember what each tool did and how – especially after you have worked a few unfamiliar tools through the same paces. Capture as much video as you can of the user experience – it will come in handy as you reach the decision point. Without further ado, let’s jump into the PoC. Testing Almost every email system (Exchange, Office 365, Google Suite, etc.) provides some means of blocking malicious email. So that is the base level for comparison. The next question becomes whether you want to take an active or passive approach during the PoC. In an active test you introduce malicious messages (known malware and phishing messages) into the environment to track whether the product or service catches messages which should be detected. A passive test uses the product against your actual mail stream, knowing it will get a bunch of spam, phishes, and attacks if you look at enough messages. To undertake an active test you need access to these malicious messages, which isn’t a huge impediment as there are sites which provide known phishing messages, and plenty of places to get malware for testing. Of course you’ll want to take plenty of precautions to ensure you don’t self-inflict a real outbreak. There is risk in doing an active test, but it enables you to evaluate false negatives (missing malicious messages), which create far more damage than false positives (flagging

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